(1R,5S,6R)-3-((E)-Hex-1-enyl)-5-hydroxy-4-hydroxymethyl-7-oxa-bicyclo[4.1.0]hept-3-en-2-one | 635678-69-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,5S,6R)-3-((E)-Hex-1-enyl)-5-hydroxy-4-hydroxymethyl-7-oxa-bicyclo[4.1.0]hept-3-en-2-one
• 英文别名: (1R,5S,6R)-3-[(E)-hex-1-enyl]-5-hydroxy-4-(hydroxymethyl)-7-oxabicyclo[4.1.0]hept-3-en-2-one
• CAS: 635678-69-2
• 化学式: C₁₃H₁₈O₄
• 分子量: 238.284
• InChiKey: QRJUHUFPQZMOKS-LXXZJSEWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  70.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  叔丁基二甲基氯硅烷 、 (1R,5S,6R)-3-((E)-Hex-1-enyl)-5-hydroxy-4-hydroxymethyl-7-oxa-bicyclo[4.1.0]hept-3-en-2-one 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 (1R,5S,6R)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-3-((E)-hex-1-enyl)-5-hydroxy-7-oxa-bicyclo[4.1.0]hept-3-en-2-one
  参考文献：
  名称：

  Novel non-peptide inhibitors targeting death receptor-Mediated apoptosis

  摘要：

  We have previously reported that ECH, (2R, 3R, 4S)-2,3-epoxy-4-hydroxy-5-hydroxymethyl-6-(1E)-propenyl-cyclohex-5-en-1-one inhibits Fas-mediated apoptosis by blocking self-activation of pro-caspase-8 in the death-inducing signaling complex (DISC). A series of ECH derivatives were asymmetrically synthesized via key synthetic intermediates obtained from lipase-catalyzed kinetic resolution. Inhibitory activities of the derivatives towards death receptor-mediated apoptosis both in type I and type 11 cells were investigated, revealing that novel non-peptide inhibitors, RKTS-33 and RKTS-34, are effective as ECH. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.08.003
• 作为产物：
  描述：

  rac-(1R,5R,6S)-3-methoxycarbonyl-7-oxabicyclo[4.1.0]hept-2-en-5-ol 在 2,6-二叔丁基-4-甲基苯酚 吡啶 、 叔丁基过氧化氢 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 二(氰基苯)二氯化钯 、 Amberlyst 15 、 bis(acetylacetonate)oxovanadium 、 三苯胂 、 Pseudomonas stutzeri lipase (Meito TL) 、 四丁基氟化铵 、 碘 、 4-甲基苯磺酸吡啶 、 戴斯-马丁氧化剂 、 三乙胺 、 [双(三氟乙酰氧基)碘]苯 、 silver(l) oxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 异丙醇 为溶剂， 生成 (1R,5S,6R)-3-((E)-Hex-1-enyl)-5-hydroxy-4-hydroxymethyl-7-oxa-bicyclo[4.1.0]hept-3-en-2-one
  参考文献：
  名称：

  Novel non-peptide inhibitors targeting death receptor-Mediated apoptosis

  摘要：

  We have previously reported that ECH, (2R, 3R, 4S)-2,3-epoxy-4-hydroxy-5-hydroxymethyl-6-(1E)-propenyl-cyclohex-5-en-1-one inhibits Fas-mediated apoptosis by blocking self-activation of pro-caspase-8 in the death-inducing signaling complex (DISC). A series of ECH derivatives were asymmetrically synthesized via key synthetic intermediates obtained from lipase-catalyzed kinetic resolution. Inhibitory activities of the derivatives towards death receptor-mediated apoptosis both in type I and type 11 cells were investigated, revealing that novel non-peptide inhibitors, RKTS-33 and RKTS-34, are effective as ECH. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.08.003

文献信息

• Novel non-peptide inhibitors targeting death receptor-Mediated apoptosis
  作者：Hideaki Kakeya、Yasunobu Miyake、Mitsuru Shoji、Satoshi Kishida、Yujiro Hayashi、Takao Kataoka、Hiroyuki Osada

  DOI：10.1016/j.bmcl.2003.08.003

  日期：2003.11

  We have previously reported that ECH, (2R, 3R, 4S)-2,3-epoxy-4-hydroxy-5-hydroxymethyl-6-(1E)-propenyl-cyclohex-5-en-1-one inhibits Fas-mediated apoptosis by blocking self-activation of pro-caspase-8 in the death-inducing signaling complex (DISC). A series of ECH derivatives were asymmetrically synthesized via key synthetic intermediates obtained from lipase-catalyzed kinetic resolution. Inhibitory activities of the derivatives towards death receptor-mediated apoptosis both in type I and type 11 cells were investigated, revealing that novel non-peptide inhibitors, RKTS-33 and RKTS-34, are effective as ECH. (C) 2003 Elsevier Ltd. All rights reserved.